SYNTHESIS OF (-)-MURICATACIN

Authors
MAKABE H TANAKA A ORITANI T
Citation
H. Makabe et al., SYNTHESIS OF (-)-MURICATACIN, Bioscience, biotechnology, and biochemistry, 57(6), 1993, pp. 1028-1029
Citations number
9
Categorie Soggetti
Biology,Agriculture,"Biothechnology & Applied Migrobiology","Food Science & Tenology
Journal title
Bioscience, biotechnology, and biochemistry → ACNP
ISSN journal
09168451
Volume
57
Issue
6
Year of publication
1993
Pages
1028 - 1029
Database
ISI
SICI code
0916-8451(1993)57:6<1028:SO(>2.0.ZU;2-Q
Abstract
The synthesis of (-)-muricatacin starting from 1-bromododecane and 2-p entyn-1-ol is described. 2-Pentadecyn-1-ol (4), which was prepared fro m 1-bromododecane (2) and 2-pentyn-1-ol (3), was converted to epoxy al cohol 6 through a two-step reaction sequence, 6 being successively sub mitted to tosylation, iodination, chain extension with tert-butyl lith ioacetate, and acid-catalyzed cyclization to give (-)-muricatacin (1a) . Recrystallization afforded optically pure 1a.